Annual Events & Festivals

Browse our listing of annual events and make your plans! From historic downtown Brooksville to area parks and the sparkling Gulf of Mexico coast, many events celebrate our pleasant Florida weather. Pick from a brimming buffet of culinary celebrations. Step back in time with historical re-enactments and watch demonstrations of other cultures and lifestyles. Explore your interests. Discover unique entertainment. Dance, shop, taste, look and listen throughout an eventful year here in Nature’s Place to Play.

Annual Events Guide Image

January

January 2, 2021

Croom Zoom Trail Run

The Croom Zoom 100K/50K/25K courses uses the extensive trails of Croom Park. The trails wind through oak hammocks on a well-defined trail that takes runners through some of the best cross-country running terrain in Florida. Tucker Hill Fire Tower Parking Lot, 26416 Croom Rd., Brooksville.

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January 4-5, 2020

AKC Dog Agility Trials

Don’t miss the ultimate in competitions as the dogs and handlers perform at their highest levels. Florida Classic Park, 5360 Lockhart Rd., Brooksville.

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January 3, 2021

Spring Hill Marathon Mania / Hand Cyclists Marathon

Marathon, Half-Marathon, 10K or 5K – this Boston Marathon Qualifier is Central Florida’s first marathon race of the year. Anderson Snow Park, 1360 Anderson Snow Rd., Spring Hill.

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January 14-24, 2021

Florida Gulf Coast Cluster AKC All-Breed Dog Show

Ten days of competitions featuring ten American Kennel Club All-Breed Dog Shows, two days of specialty shows, Conformation, Junior Showmanship, Obedience and Rally Trials, plus visits with the dogs and their handlers. Florida Classic Park, 5360 Lockhart Rd., Brooksville.

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January 2021

Florida Agriculture & Wildlife Expo

A showcase of Hernando County’s finest agriculture, wildlife, arts, talent, and industry, plus crafts and entertainment. Brooksville-Tampa Bay Regional Airport, Runway Drive entrance (off US-41 S), Brooksville.

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January 2020

Hernando County Greek Festival

Enjoy Greek food and pastries, music, traditional folk dance (with lessons), a toga run, kids’ zone, cooking demonstrations, arts and craft vendors and more. Christ the Savior Greek Orthodox Church, 10401 Spring Hill Drive, Spring Hill.

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February

February 6, 2021

Moon Over Croom – 21M, 14M, 7M Trail Run

Experience Croom like you never have before; running in the dark. The main day-run trail is a well-marked 7-mile loop; glow sticks will mark the course for night. Tucker Hill Fire Tower Lot, 26416 Croom Rd., Brooksville.

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February 6-7, 2021

Brooksville Native American Festival

The family-friendly festival features authentic dancing and music, artists and craftsmen from around the country, primitive skills demonstrations, and Native foods like fry bread and buffalo burgers. Florida Classic Park, 5360 Lockhart Rd., Brooksville.

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February 7-8, 2020

Celtic Family Jamboree

A unique family-friendly Celtic experience sharing tradition through live performance, workshops and crafts. Sertoma Youth Ranch, 85 Myers Rd., Brooksville.

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February   2021

Heritage Day

A celebration of 1800’s Hernando County, including historic home tours, carriage rides, museum tours, crafts and heritage activities for all ages. May-Stringer Historical Museum, 601 Museum Court, Brooksville.

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February 18-23, 2020

Florida Bluegrass Classic

Enjoy five days of live Bluegrass and Classic Country performers, including TG Sheppard, Penny Creek, Big Cypress and more! Florida Classic Park, 5360 Lockhart Rd., Brooksville.

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February 27, 2021

Tin Can Tourists Winter Convention Open House

Tin Can Tourists celebrate the preservation of classic Gulfstream camping trailers and motor coaches dating from the 1940’s to the 1960’s. The TCT Open House is from 11am – 3pm. Sertoma Youth Ranch, 85 Myers Rd., Brooksville.

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March

March 5-7, 2021

Weeki Wachee Swamp Fest
(Virtual 2021 Event)

One of the premier fine arts, crafts and music festivals in the southeast includes the Swamp Monster contest and over 140 vendors and crafters, entertainment, live bands including country, folk, and toe-tapping get-up-and-dance tunes. Linda Pedersen Park, 6300 Shoal Line Blvd., Weeki Wachee.

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March 12-14, 2021

The Will McLean Music Festival

Named for the Father of Florida Folk Music, this festival features entertainment by Florida’s singers and songwriters, including workshops, arts, crafts, poetry reading, storytelling, and children’s activities. Sertoma Youth Ranch, 85 Myers Rd., Brooksville.

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March 13-14, 2021

Art in the Park: Art, Crafts & Music Festival

The Gulf Coast’s largest Art Festival with over 115 artisans participating in the annual juried show featuring fine art, fine craft, craft artist vendors, student art, and live entertainment. Tom Varn Park, 306 Darby Ln., Brooksville.

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March 19-21, 2021

Blues Bash at The Ranch

Enjoy Hot Blues – Cool Nights at this new 3-day music festival. Music, workshops, family and dog-friendly. Choose to camp or buy a day pass at Sertoma Youth Ranch, 85 Myers Rd., Brooksville.

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March 24-27, 2021

Spring Bluegrass Festival

Enjoy four days of the best in Bluegrass music, stage shows, open mic, workshops, movies, children’s activities, and a Sunday morning Gospel Sing. Sertoma Youth Ranch, 85 Myers Rd., Brooksville.

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March 27-28, 2021

Central Florida Sportsman’s Expo

Calling all outdoor enthusiasts. From fishing to boating, kayaking, ATVing and RVing, celebrate the outdoor adventurous lifestyle at the inaugural Central Florida Sportsman’s Expo. Tour vendors, view demonstrations and much more at Brooksville’s beautiful Tom Varn Park.

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April

April 8-11, 2021

Stringbreak Music Festival

This multi-stage Americana music fest features Roots Rock, Alternative Country, Newgrass and Bluegrass. Camping, vendors, and well-planned activities make for a great weekend. Sertoma Youth Ranch, 85 Myers Rd., Brooksville.

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April 2021

Hernando County Fair

You know it’s Spring when the Fair is here! The whole family will enjoy exhibits, Midway rides, games, livestock shows, vendors, food and live entertainment, including evening shows. Hernando County Fairgrounds, 6436 Broad St. (US-41S), Brooksville.

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April 2021

Brooksville Blueberry Festival

All things blueberry take over historic downtown Brooksville the last weekend of April each year. Filled with family friendly fun, music and food, it’s known as the Best Little Festival in Florida. Historic downtown Brooksville.

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May

May 1, 2021

John Holmes 50K, 16M, 9M Trail Run

The John Holmes is the Grand Daddy of 50Ks being the oldest trail run in Florida. This is a classic loop course with 7 mile loops. A beautiful course that winds through the oak and scrub forest of Croom – a must for anyone looking to try a 50K. Tucker Hill Fire Tower Lot, 26416 Croom Rd., Brooksville.

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Weekends in May

Sunflower Maze, Spring Crops and Farm Activities

Maze your way through the paths of 8 to 10-foot-tall sunflowers in search of the exit. Six acres of fun, including hay rides, picnic area, family activities and spring produce. Sweetfields Farm, 17250 Benes Roush Rd., Masaryktown.

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May 13-17, 2020

Orange Blossom Jamboree

This family-friendly music festival features an outdoor pavilion and three stages for continuous entertainment with more than 60 bands. Sertoma Youth Ranch, 85 Myers Rd., Brooksville.

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June

July

First Saturday in July

Scallop Season Opens

Grab your snorkel gear and Diver-down flag and head for the water! The much-anticipated annual scallop season opens and runs into September. Bayport Park, 4140 Cortez Blvd., Brooksville or Hernando Beach Boat Ramp, 4483 Calienta St., Hernando Beach.

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August

August 13 – 15, 2021

The Spirit of Woodstock Music Festival

Set in the rolling hills of Brooksville’s Sertoma Youth Ranch, Spirit of Woodstock Music Festival is a camping optional experience you don’t want to miss. With over 80 acres of oak trees, a creek and lake, the picturesque setting is ideal for this family – and pet-friendly – event. Camp or buy single day tickets.

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September

September 19, 2020

Olive Grove Mill Party Weekend

Tour the Orchard, Sample Our Fresh Oil and Olive Products,  See our Mill Produce Fresh Extra Virgin Olive Oil.  Workshops! Food! Beverages! Live entertainment!

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September 26, 2020

Hernando Bar 5K 10K

This 7th Annual Run is comprised of five year age groups, three deep, plus Master’s Division and Overall Winners and Fastest Lawyer. Weekiwachee Preserve 2345 Osowaw Boulevard, Spring Hill

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OCTOBER

Weekends in October

Fall RoundUp Farm Fun

Enjoy mazes, hayrides, entertainment, family activities, storytelling, games, produce barn and more. Sweetfields Farm, 7250 Benes Roush Rd., Masaryktown.

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October 5, 2020

Papa Joe’s Annual Pasta Fest

The first Tuesday in October, bring your appetite to the 99¢ All-You-Can-Eat pasta event with children’s activities and entertainment. Papa Joe’s Italian Restaurant, 6244 Spring Lake Hwy., Brooksville.

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Weekends in October

Fall Corn Maze and Farm Activities

Enjoy the corn and other mazes, hayrides, entertainment, family activities and more. Harvest Moon Farm, 15990 Stur St., Masaryktown.

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October 16-18, 2020

Camping with the Blues

Enjoy three days and three nights of “Blues Under the Stars With The Stars Of The Blues.” Sertoma Youth Ranch, 85 Myers Rd., Brooksville.

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October 17, 2020

Mud Endeavor, Castle Canyon

Make some new friends, achieve some new goals and create new memories! This premium course resides on over 100 acres of untouched valleys with unbeaten trails and breathtaking cliffs. Castle Canyon is the site of a rock mining operation that took place in the 1920’s. 10444 Beggs Lane, Brooksville

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October 24, 2020

Halloween Haunted House

Enjoy spooky hauntings and a fun-filled evening of children’s games, face painting, story-telling, roasting marshmallows around the bonfire, and more! May-Stringer House Historical Museum, 601 Museum Court, Brooksville.

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October 10 – 17,  2020

Founders’ Week Celebration

Celebrating the 164th anniversary of the founding of Brooksville, the entire family will enjoy a variety of events throughout the week. Throughout Historic Brooksville, 20 N. Main Street Area, Brooksville.

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October 2020

Rocky Horror Picture Show with Live Cast at the Olive Grove Fall Harvest Festival

Enjoy a meatloaf dinner and an interactive performance of  “The Rocky Horror Picture Show.” Costumes welcome! The Olive Grove, 15016 Rester Dr., Brooksville.

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October 31, 2020

Spring Lake Memorial Classic

The annual run and walk wind through scenic terrain, including a nature trail through the woods, a horse barn and up and down some challenging hills! The ARC Nature Coast, 5283 Neff Lake Rd., Brooksville.

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November

November 14, 2020

Croom 50M/50K/16M Fools Trail Run

The beautiful and challenging 50-mile course follows three repeat loops on the Croom Hiking Trail, through central Florida’s long leaf pines and scrub oak covered hills, past creek bottoms and cypress ponds. Tucker Hill Fire Tower Lot, 26416 Croom Rd., Brooksville.

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November 12-15, 2020

Riverhawk Music Festival

Four days of incredible music and entertainment, workshops and jam sessions. The eclectic array of music, includes Americana, Bluegrass, Jamgrass, Celtic, Newgrass, Cajun and more. Sertoma Youth Ranch, 85 Myers Rd., Brooksville.

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November 21 – 22, 2020

Field of Dreams Car Show

The show features street rods, rat rods, classics, four-wheel drives, modern muscle, performance vehicles and more. Plus, visit the Car Corral, swap meet, arts and crafts vendors and enjoy great food and live entertainment. Florida Classic Park, 5360 Lockhart Road, Brooksville.

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November 23 – December 7, 2020

Festival of Trees

A beautiful collection of decorated Christmas trees created by local businesses and organizations in the City of Brooksville. Open to the public for viewing and silent auction to bid on decorated trees.

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November 26-28, 2020

Thanksgiving Bluegrass Festival

Enjoy Thanksgiving dinner, camping, bluegrass and more. Sertoma Youth Ranch, 85 Myers Rd., Brooksville.

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November 2020

Taste of the Fields

A fabulous feast, from appetizers to desserts, prepared from local harvests by local chefs; served on the picturesque lawn of historic Chinsegut Hill. Chinsegut Hill Retreat, 22495 Chinsegut Hill Rd., Brooksville.

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December

December 2020

Holiday Season Carriage Rides

During four holiday evenings, enjoy traditional carriage rides around historic downtown Brooksville. View festive shops and decorations, including the spectacular 30 foot courthouse Christmas tree.  20 N. Main St., Brooksville. Reservations required.

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December 3, 2020

Downtown Brooksville’s Christmas Tree Lighting and Christmas on Main Street, an STS Top 20 Event.

Named a Southeast Tourism Society “STS Top 20 Event,” the Brooksville Main Street organization proudly presents the dazzling Christmas tree lighting event at 20 North Main Street in historic downtown Brooksville. Join attendees from around the region to hear live music, shop and eat downtown among the festive scenery.

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December 5 and 12, 2020

Annual Downton Abbey Christmas

Downton Abbey comes to life on Florida’s Adventure Coast where Lady Grantham will learn there is never a dull moment on a weekend in Brooksville! The Tilted Teacup Tea Room & Boutique, 103 S. Saxon Ave., Brooksville.

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December 5, 2020

Hilly Hundred

Join this large group of cycling enthusiasts on a challenging, invigorating group ride through Florida’s Adventure Coast’s scenic countryside. Organized by Crank Works Bicycles, this is a free (self-supported) ride with voluntary donations encouraged for different local charities.

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December 12, 2020

Kiwanis Christmas Parade

One of the largest and most colorful holiday parades in Florida kicks off at 10am, followed by special activities and shopping in the historic downtown. Historic Brooksville, 20 N. Main St., Brooksville.

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December 17, 2020

Chamber Golf Classic

Join the 28th Annual Chamber Golf Classic at Southern Hills Plantation. 4200 Summit View Drive, Brooksville.

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December 2020

May-Stringer House Night of Lights Tour

Tour this Victorian Mansion after dark, festively lit for teh holiday season. Historic Brooksville, 601 Museum Court, Brooksville.

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